Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-12 15:06:41 UTC
Update Date2020-02-26 21:26:48 UTC
HMDB IDHMDB0006823
Secondary Accession Numbers
  • HMDB06823
Metabolite Identification
Common Name2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine
Description2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. triphosphate by GTP cyclohydrolase I . 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine is a strong basic compound (based on its pKa). 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine exists in all living organisms, ranging from bacteria to humans. Within humans, 2,5-diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine participates in a number of enzymatic reactions. In particular, 2,5-diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine can be biosynthesized from 2,5-diaminopyrimidine nucleoside triphosphate through its interaction with the enzyme GTP cyclohydrolase. In addition, 2,5-diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine can be converted into dihydroneopterin triphosphate through the action of the enzyme GTP cyclohydrolase. In humans, 2,5-diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine is involved in pterine biosynthesis. 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidine can be converted into 2-Amino-4-hydroxy-6-(erythro-1,2,3-trihydroxypropyl)dihydropteridine.
Structure
Data?1582752408
SynonymsNot Available
Chemical FormulaC9H18N5O14P3
Average Molecular Weight513.1856
Monoisotopic Molecular Weight513.006309845
IUPAC Name[({[({5-[(2,5-diamino-6-oxo-3,6-dihydropyrimidin-4-yl)amino]-2,3-dihydroxy-4-oxopentyl}oxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]phosphonic acid
Traditional Name[({5-[(2,5-diamino-6-oxo-3H-pyrimidin-4-yl)amino]-2,3-dihydroxy-4-oxopentyl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
NC1=NC(=O)C(N)=C(NCC(=O)C(O)C(O)COP(O)(=O)OP(O)(=O)OP(O)(O)=O)N1
InChI Identifier
InChI=1S/C9H18N5O14P3/c10-5-7(13-9(11)14-8(5)18)12-1-3(15)6(17)4(16)2-26-30(22,23)28-31(24,25)27-29(19,20)21/h4,6,16-17H,1-2,10H2,(H,22,23)(H,24,25)(H2,19,20,21)(H4,11,12,13,14,18)
InChI KeyZJYBJXKSWQPKFW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose-5-phosphate
  • Monosaccharide phosphate
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Phosphoric acid ester
  • Beta-hydroxy ketone
  • Pyrimidine
  • Acyloin
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Alpha-hydroxy ketone
  • Heteroaromatic compound
  • Vinylogous amide
  • 1,2-diol
  • Secondary alcohol
  • Ketone
  • Secondary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.42 g/LALOGPS
logP-0.86ALOGPS
logP-6.2ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.89ChemAxon
pKa (Strongest Basic)3.72ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area322.88 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity105.24 m³·mol⁻¹ChemAxon
Polarizability38.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kaj-3695200000-3a55935f0cd1e0f2f9efSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-004i-2194102000-c52d41bf51dcab1f48f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-1442920000-fe5a369793012336651cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w2c-1941200000-110e7623a57abfccc156Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-5910000000-57cceddb7b071bdbb766Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0492220000-7b3e1f682e2fbbb3c9a5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057l-9560000000-056e90117fa787c6136eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-9620000000-81675245a86543331ea4Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024103
KNApSAcK IDNot Available
Chemspider ID389753
KEGG Compound IDC06148
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440923
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDHC01710
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in GTP cyclohydrolase I activity
Specific function:
Positively regulates nitric oxide synthesis in umbilical vein endothelial cells (HUVECs). May be involved in dopamine synthesis. May modify pain sensitivity and persistence. Isoform GCH-1 is the functional enzyme, the potential function of the enzymatically inactive isoforms remains unknown.
Gene Name:
GCH1
Uniprot ID:
P30793
Molecular weight:
27902.855
Reactions
Dihydroneopterin triphosphate + Water → 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidinedetails
2,5-Diaminopyrimidine nucleoside triphosphate → 2,5-Diamino-6-(5'-triphosphoryl-3',4'-trihydroxy-2'-oxopentyl)-amino-4-oxopyrimidinedetails